Capturing a sulfenic acid with arylboronic acids and benzoxaborole

C. Tony Liu, Stephen Benkovic

Research output: Contribution to journalArticlepeer-review

30 Scopus citations


Post-translational redox generation of cysteine-sulfenic acids (Cys-SOH) functions as an important reversible regulatory mechanism for many biological functions, such as signal transduction, balancing cellular redox states, catalysis, and gene transcription. Herein we show that arylboronic acids and cyclic benzoxaboroles can form adducts with sulfenic acids in aqueous medium and that these boron-based compounds can potentially be used to trap biologically significant sulfenic acids. As proof of principle we demonstrate that a benzoxaborole can inhibit the enzyme activity of an iron-containing nitrile hydratase, which requires a catalytic αCys114-SOH in the active site. The nature of the adduct and the effect of the boronic acid's pKa B on the stability constant of the adduct are discussed within.

Original languageEnglish (US)
Pages (from-to)14544-14547
Number of pages4
JournalJournal of the American Chemical Society
Issue number39
StatePublished - Oct 2 2013

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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